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Org Biomol Chem. 2012 Oct 28;10(40):8147-53.

Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue.

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1
School of Applied Sciences [Applied Chemistry], RMIT University, Bowen Street, Melbourne, Vic. 3001, Australia.

Abstract

The first synthesis of a lactam analogue of salicylihalamide A (1) is reported. A key step in the approach was a photochemical acylation coupling between amine 10 and dioxinone 9 to form the amide 19. Acetylation followed by RCM with Grubbs 1st generation catalyst gave the desired E-lactam 23 (E : Z ratio 87 : 13) as the major compound. Conversion of macrolactam 23 into the vinyl iodide 26 followed by Cu catalysed cross coupling with the diene amide 7 gave aza-salicylihalamide analogue 3 in good yield. This compound demonstrated potent activity against several human leukaemia cell lines.

PMID:
22964776
DOI:
10.1039/c2ob26649k
[Indexed for MEDLINE]
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